Allyl bromide → 2,6,6-Trimethyl-1-(1-hydroxy-3-butenyl)-1-cyclohexene

Participants

Reaction Steps

In a typical experiment 10.7 g. of Mg turnings and 5 g. of allyl bromide were allowed to react in 7: ml. of dry ether. The reaction was exothermic and the temperature of the reaction mixture increased up to the boiling point of the solvent. To this solution allyl bromide (46 g.) and β-cyclocitral (61 g.) in 160 ml. of ether were added with vigorous stirring at such a rate as to maintain the ether at the boiling temperature. The reaction mixture was then kept at reflux during 6 hours and after cooling it was poured into a ice-cold concentrated aqueous solution of NH4Cl. The ethereal layer after the usual treatment gave 2,6,6-trimethyl-1-[1-hydroxy-3-butenyl]-1-cyclohexene (44.5 g.; 57% yield): B.p. 60°-2°/0.001 Torr; nD20 =1.4964; d420 =0.9.

Provenance & Evidence